U.S. patent number 4,132,657 [Application Number 05/719,518] was granted by the patent office on 1979-01-02 for treatment of metal surfaces.
This patent grant is currently assigned to GAF Corporation. Invention is credited to Louis J. Nehmsmann, III, Robert J. Verdicchio.
United States Patent |
4,132,657 |
Verdicchio , et al. |
January 2, 1979 |
Treatment of metal surfaces
Abstract
Complex phosphate ester surfactants derived from a quaternary
dihydroxy compound having the formula ##STR1## wherein R and
R.sub.1 represent the same or different alkyl moieties containing 1
to 22 carbon atoms, the sum of R and R.sub.1 not being less than 7
carbon atoms; R.sub.2 and R.sub.3 each represent H or CH.sub.3 ; n
is an integer having an average value of from 1 to 50; X is an
anion of halogen, sulfate, or alkyl sulfate; and wherein the
resultant complex phosphate ester contains at least 1/3 P atom per
mole of quaternary dihydroxy compound; can be made through reaction
of such dihydroxy quaternary compound with a conventional
phosphating agent such as P.sub.2 O.sub.5, polyphosphoric acid, or
POCl.sub.3 to form interesting amphoteric surface active agents
having utility as metal lubricants, heavy duty cleaners,
detergents, etc.
Inventors: |
Verdicchio; Robert J.
(Succasunna, NJ), Nehmsmann, III; Louis J. (Ellicott City,
MD) |
Assignee: |
GAF Corporation (New York,
NY)
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Family
ID: |
26996285 |
Appl.
No.: |
05/719,518 |
Filed: |
September 1, 1976 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
Issue Date |
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557043 |
Mar 10, 1975 |
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349649 |
Apr 9, 1973 |
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Current U.S.
Class: |
508/389; 508/425;
508/428; 558/158; 558/169 |
Current CPC
Class: |
C11D
1/88 (20130101); B01F 17/0064 (20130101); C10M
173/02 (20130101); C23F 11/1673 (20130101); C11D
1/886 (20130101); C10M 2207/121 (20130101); C10N
2050/01 (20200501); C10M 2215/04 (20130101); C10M
2223/042 (20130101); C10M 2223/04 (20130101); C10M
2219/042 (20130101); C10N 2010/06 (20130101); C10M
2207/122 (20130101); C10N 2040/08 (20130101); C10M
2225/00 (20130101); C10M 2219/044 (20130101); C10M
2225/02 (20130101); C10M 2201/02 (20130101); C10M
2215/26 (20130101); C10N 2040/46 (20200501) |
Current International
Class: |
C23F
11/167 (20060101); C23F 11/10 (20060101); B01F
17/00 (20060101); C10M 173/02 (20060101); C11D
1/88 (20060101); C10M 001/48 (); C07F 009/09 () |
Field of
Search: |
;260/929
;252/32.5,32.7E,33,46.7,49.9 |
References Cited
[Referenced By]
U.S. Patent Documents
Foreign Patent Documents
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813502 |
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Oct 1974 |
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BE |
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2416018 |
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Oct 1974 |
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DE |
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355457 |
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Aug 1961 |
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CH |
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465200 |
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Apr 1937 |
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GB |
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Primary Examiner: Sutto; Anton H.
Attorney, Agent or Firm: Kehm; W. C. Dresner; A. Ward; J.
J.
Parent Case Text
CROSS-REFERENCE TO RELATED APPLICATIONS
This is a continuation-in-part of application Ser. No. 557,043,
filed Mar. 10, 1975, now abandoned, which, in turn, was a
continuation of application Ser. No. 349,649, filed Apr. 9, 1973
and now abandoned.
Claims
We claim:
1. A method comprising treating a steel surface with a lubricating
composition containing an effective lubricating amount of an
amphoteric surface active agent of the formula: ##STR9## wherein R
is C.sub.6-22 alkyl, R.sub.1 is C.sub.1-2 alkyl or benzyl,
y.sub.1 and y.sub.2 are each integers of 1-50,
Z.sub.1 is, with the bonded O atom, a phosphate ester group in free
acid form or in the form of its sodium, potassium, calcium or
magnesium salt,
Z.sub.2 is H or Z.sub.1, and
A is a halogen, sulfate or C.sub.1-2 alkyl sulfate anion.
2. A method as defined in claim 1 in which Z.sub.1 is in the form
of the Na salt.
3. A method as defined in claim 1 wherein the sum of y.sub.1 and
y.sub.2 is 5-50.
4. A method as defined in claim 1 wherein R is derived from
cocoamine.
5. A method as defined in claim 1 wherein R is derived from
tallowamine.
6. A method as defined in claim 1 wherein R is derived from
oleylamine.
7. A method as defined in claim 1 wherein R is derived from
stearylamine.
Description
BACKGROUND OF THE INVENTION
Field of the Invention
This invention relates to new amphoteric surfactants, and more
particularly to specific ethyoxylated amines which are quaternized
and at least partially phosphated; methods of making such
surfactants; and to methods of using such surfactants. More
particularly, this invention relates to novel complex phosphate
surfactants that are derived from quaternary dihydroxy compounds of
the formula ##STR2## WHEREIN R and R.sub.1 represent the same or
different alkyl moieties containing 1 to 22 carbon atoms, the sum
of R and R.sub.1 not being less than 7 carbon atoms; R.sub.2 and
R.sub.3 each represent H or CH.sub.3 ; n is an integer having an
average value of from 1 to 50; X represents an anion of halogen,
sulfate, or alkyl sulfate; and wherein the resultant complex
phosphate ester contains at least 1/3P atom per mole of quaternary
dihydroxy compound; can be made through reaction (phosphating) of
such dihydroxy quaternary compound with a conventional phosphating
agent such as P.sub.2 O.sub.5, polyphosphoric acid, or POCl.sub.3
to form amphoteric surface active agents having utility as metal
lubricants, heavy duty cleaners, detergents, etc.
In particular, the ultimate complex phosphate ester surfactants
themselves, that are derived from phosphating in the manner
discussed above, are compositions which are characterized by the
following chemical formula or structure ##STR3## wherein R and
R.sub.1 represent the same or different alkyl moieties containing 1
to 22 carbon atoms, the sum of the total number of carbon atoms for
R and R.sub.1 not being less than 7; R.sub.2 and R.sub.3 each
represent H or CH.sub.3 ; n is an integer having an average value
of from 1 to 50; ##STR4## where R.sub.2 and R.sub.3 are as
previously defined; Y is a moiety of OH, ##STR5## (a triester), p
being an integer of at least 1, M being H or a metal cationic
equivalent thereof such as that of Na or K and being as previously
defined; Z is a moiety of OH, ##STR6## p being an integer of at
least 1, M being a metal cationic equivalent thereof (e.g., Na or
K) and L being as previously defined; and X is an anion such as,
e.g., halogen, sulfate, or alkyl sulfate, etc. Of course, as would
be appreciated by those skilled in the art, the diesters and
triesters of the above formula can exist in a variety of forms,
e.g., in the form of a variety of aliphatic, cyclic, and polymeric
compounds. However, in accordance with the present invention, the
major products formed comprise aliphatic monoesters and
diesters.
Description of the Prior Art
The prior art describes many, and varied, types of amine
phosphonates, phosphates, and related compounds. For example,
various hydroxy alkyl and dihydroxyl alkyl derivatives of higher
fatty acid amines have been phosphated, but none of these compounds
have achieved significant commercial acceptance and in none have
been found all of the desirable properties of the instant
invention.
Considerable research has been carried out during the past few
years directed towards improving the lubricating and rust and
corrosive inhibiting properties of the new synthetic surfactant
compositions. Most of these surfactant compositions have, as active
surfactant ingredient, anionic ions. As representative of the
various additives which have been employed for improving the
detersive and surfactant properties of such anionic compositions,
there may be mentioned alkali metal phosphates, borates,
carbonates, sulfates, chlorides, silicates, higher aliphatic
alcohols such as lauryl alcohol, and higher fatty acid amides and
alkylol amides such as lauroyl amide, lauroyl mono and dialkyl
amides, lauroyl ethanolamide, and lauroyl di-ethanolamide. The use
of the aforementioned alkali metal salts, particularly the
phosphates and borates, generally have resulted in what is known as
built or heavy duty type detergents. While such compositions are
partially suitable for use in cleaning machines of various types,
they find limited use in applications wherein any degree of metal
lubrication and cleaning is involved. However, these additives,
which have thus far been more or less commercially accepted have
properties and characteristics which still leave much to be desired
with respect to characteristics such as more universal
compatibility and adaptability to different conditions, cost and
the like.
Various organic surfactants have achieved considerable commercial
success; however, the art is still confronted by the problem of
providing surfactant compositions which provide dual cationic and
anionic functionalities and yet are free from undesirable
disadvantages.
It has been found that the compositions according to the instant
invention comprise very valuable surface-active agents which may be
used either alone or admixed with other cationic, anionic or
non-ionic surface active agents in the different fields as above
referred to.
The instant compositions comprise a very valuable group of
surface-active agents, known as amphoteric compounds, i.e.,
chemical agents containing both cationic and anionic groups in a
single molecule, and therefore exhibit a high degree of stability
and remarkable utility in concentrated electrolytic solutions.
These compounds also show unusual chemical stability under
prolonged contact with alkaline systems. Products made from the
instant compounds have the following advantages: they possess good
surface-active properties so that they can be used as detergents
since they have the advantage of preventing the accumulation of
electrostatic charges, are well tolerated by the skin and,
therefore, do not cause any appreciable irritation thereto, are
useful as lubricants, rust inhibitors, corrosion inhibitors, hard
surface cleaners, alkali soluble cleaners, agriculture emulsifiers,
hydraulic fluids, and in emulsion polymerization.
These amphoterics employ the phosphate ester as the anionic moiety,
thereby in addition to providing dual cationic/anionic
functionality, offer novel properties such as metal lubrication,
and cleaning, enhanced corrosion inhibition and alkali
solubility.
The novel compounds of this invention have the following unexpected
combinations of properties: (1) they, unlike phosphates of
ethoxylated amines, tolerate the presence of chlorine bleaches; (2)
they may be used in shampoos and other cosmetics at pH values of
4.5-8.5 and under these conditions are effective cleaning agents
whereas conventional counterparts to these materials do not work
well under pH values of 6.0:conventional amphoterics such as
betaines do not work at their isoelectric point (about pH 5.7)
since they become insoluble at these pH values; (3) they are better
detergents with average or hard water; do not precipitate; at pHs
as low as 4.5 they are mild to the eyes and skin and they are
relatively non-toxic. In addition, these products are readily
biodegradable and as such are ecologically safe. The instant
amphoteric compounds are useful as detergents, wetting, emulgating
and emulsifying agents and also possess a unique combination of
properties which will provide new and improved products for
lubricants, pesticide emulsifiers, hard surface cleaners, etc. They
are also useful as surface active agents in treating natural and
synthetic fibers in the textile and related fields where they may
be employed as synthetic detergents, dye assistants and
softeners.
These amphoteric surfactants also show an advantage over the prior
art and seemingly do not exhibit a pronounced isoelectric point
where general surface-active and physical properties such as
solubility, foaming, etc. are at a minimum.
SUMMARY OF THE INVENTION
It is an object of the instant invention to avoid one or more
drawbacks of the prior art.
It is another object of the invention to provide an improved
composition for the wet treatment of materials.
It is still another object of the invention to provide for
amphoteric chemical compositions that may be used in aqueous
solutions at acid neutral or alkaline pH. In the former, they serve
as cationic surface-active agents; in the latter, as anionic
surface-active agents.
It is still a further object of the invention to provide for new
articles of manufacture, such as surface-active compositions, rust
and corrosion inhibitors, hard surface cleaners, agricultural
emulsifiers, pesticide emulsifiers, wetting agents, lubricants and
fabric softeners.
These and other objects of the invention will become more apparent
as the description proceeds.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
As previously noted, the present complex phosphate surfactants are
derived from quaternary dihydroxy compounds previously described
above, and, as derived, are obtained in two major forms: (1) as
monoesters, and (2) as diesters, with minor amounts of triesters
(essentially as an impurity) being formed.
The cation M, as utilized herein and in the formula of the present
amphoteric compounds set forth on page 3, represents H or a
conventional cation such as: Na, K, Mg, Ca, Al, preferably Na or K,
or a suitable amine such as an alkanol amine or alkylamine,
preferably monoethanolamine, diethanolamine, or triethanolamine.
The X moiety of the quaternary dihydroxy compound, when a halogen,
may be chlorine, fluorine, bromine, or iodine and preferably
chlorine. When a sulfate, X can be an alkyl sulfate, preferably
ethyl sulfate. In the most preferred embodiment, R and R.sub.1 are
dissimilar, one being a long alkyl chain, the other being a shorter
alkyl chain, the sum total of carbon atoms for R and R.sub.1, taken
together, not being less than 7 carbon atoms. Also disclosed are
methods of making same and uses therefor.
From the above description, and as more fully described hereafter,
it will be apparent that the preferred embodiment of this invention
relates to a method comprising treating a metal surface with a
metal-cleaning, -lubricating and -rust and -corrosion inhibiting
composition containing an effective amount of an amphoteric surface
active agent of the formula: ##STR7## wherein R is C.sub.6-22
alkyl, R.sub.1 is C.sub.1-2 alkyl or benzyl,
y.sub.1 and y.sub.2 are each integers of 1-50,
Z.sub.1 is, with the bonded O atom, a phosphate ester group in free
acid form or in the form of its sodium, potassium, calcium or
magnesium salt,
Z.sub.2 is H or Z.sub.1, and
A is a halogen, sulfate or C.sub.1-2 alkyl sulfate anion.
The novel compounds of the instant invention may be prepared from a
precursor material by first condensing an alkyl amine, containing 6
to 22 carbon atoms in its alkyl chain, with an alkylene oxide (e.g.
ethylene oxide or propylene oxide) in the presence of a
conventional base. To produce the quaternized component, a
quaternizing agent is added thereto and the alkoxylated amine is
thereafter quaternized. The quaternized alkoxylated amine is
thereafter phosphated so as to produce a quaternary phosphate. The
phosphated amphoteric product is generally a mixture containing
varying amounts of monophosphate, diphosphate, triphosphate,
non-phosphated nonionic (alkoxylate), phosphoric acid, and minor
amounts of other materials such as polymers of the foregoing
phosphates.
The alkyl portion of the amine can be replaced by equivalent
unsaturated moieties, i.e., alkenyl groups. A pure source of alkyl
amine to be employed can vary in carbon length from 6 to 22 carbon
atoms; examples of pure saturated acids which can be used as
precursors for such an amine are caproic, caprylic, capric, lauric,
myristic, palmitic, stearic, arachidic, and behenic. Unsaturated
pure fatty acid precursors include those such as oleic lauroleic,
palmitoleic and ricinoleic. Mixtures of the above fatty acids,
commonly found in vegetable oils, animal fats and oils, and the
marine fats and oils, may also be used successfully as precursors.
Examples of vegetable sources of useful precursor fatty acids
containing mixtures in various proportions are coconut oil, linseed
oil, olive oil, palm oil, peanut oil, tung oil, and rape seed oil.
Animal and marine sources of fatty acids containing saturated and
unsaturated fatty acid substituents are lard, tallow, and sardine
oil. Any fatty acid or mixtures of fatty acids whether pure or from
impure sources may be employed as an amine precursor without
departing from the spirit of the invention so long as they contain
from 6 to 22 carbon atoms in their chain length.
Preferred fatty acids are those contained in coconut vegetable oil.
A typical coconut vegetable oil may contain fatty acids varying in
length from 8 to 18 carbon atoms. These fatty acids from coconut
oil can be saturated or unsaturated.
The alkyl amines used in this invention can also be derived from
the esters of the fatty acids without departing from the scope of
the invention. The methyl or ethyl esters of the fatty acids can be
easily condensed with the polyamines of substituted polyamines with
ready removal of methanol or ethanol occurring.
The fatty acid amine precursor is prepared in accordance with
procedures well known in the art and, accordingly, that reaction
and reaction product per se, form no part of the instant
invention.
The thus-produced alkyl amine is then subjected to an alkoxylation
reaction in accordance with procedures well known in the art, such
as, for example, by reacting the amine with the required number of
moles of ethylene oxide to produce the ethyoxylated amine employed
in the instant invention. This oxyethylation reaction is well known
in the art and fully described in U.S. Pat. No. 1,970,578 and in
many other patents. The reaction is preferably carried out at
elevated temperatures and pressures, and may be catalyzed by
quaternary hydroxides, amines, acids and/or coordinating type
compounds, although strong alkaline catalysts such as KOH or NaOH
and the like are preferred because of the fewer by-products formed
and the more easily controllable reaction conditions under which
they can react. Since the reaction is substantially quantitative,
the molecular proportions of the ethylene oxide and amine employed
determine the average oxyethylene chain length of the resulting
ethoxylated amine, although it will be understood that the product
is a mixture of ethoxylated amines of varying oxyethylene chain
length. As stated above, sufficient ethylene oxide is employed to
produce an ethoxylated amine containing by weight about 25 to 90
percent of combined ethylene oxide. The optimum oxyethylene chain
length will in any particular instance be determined mainly by the
particular amine being oxyethylated, the particular detergent with
which it is to be admixed, the hardness of the water in which the
detergent is to be employed, the desired efficacy of the finished
product for the particular application, and the like.
Throughout the specification, the invention is described with
reference to the phosphated quaternized alkoxylated amine. It is to
be understood, however, that the amine as well as the alkoxylated
amine are products known in the art. The alkoxylated amine may be
used per se or the amine may be alkoxylated in accordance with
procedures well known in the art.
The product of the invention is then conveniently prepared by
reacting appropriate proportions of alkoxylated monoalkyl amine in
the presence of said hypophosphorous acid and a quaternizing agent,
such as diethylsulfate, the latter being present in the amount of
50 to 100 mole %, preferably 90 to 100 mole %.
The alkoxylated monoalkyl amine starting materials prepared by
alkoxylating primary amines, have the general structure ##STR8##
wherein R.sub.2 and R.sub.3 are H or CH.sub.3 as above described
and n is a positive integer having an average value of from 1-50,
compounds with n=2 to 15 being preferred.
After completion of the reaction, the alkoxylated monoalkyl amine
is thereafter submitted to treatment conducive to quaternization of
the tertiary amino group, utilizing a conventional quaternizing
agent. Thus, noting the above structural formula, suitable
quaternizing agents include: dialkyl sulfates, e.g., dimethyl
sulfate, diethyl sulfate, etc.; benzyl or substituted benzyl
halides, e.g. benzyl chloride, benzyl bromide, benzyl iodide, etc.;
alkyl halides, e.g. methyl chloride, etc. Accordingly, any
conventional quaternizing agent can be advantageously employed in
the production of the quaternary alkoxylated monoalkyl amines used
herein.
The above quaternized composition is then preferably but not
necessarily stipped of any unreacted quaternizing agent and
thereafter reacted with a phosphating agent so as to convert the
quaternized alkoxylated monoalkyl amine into a quaternized
phosphate ester product. Suitable phosphating agents include
phosphorus pentoxide; polyphosphoric acid; phosphorus oxychloride;
mixtures thereof; and the like.
In accordance with a preferred procedure of the present invention,
the alkoxylated fatty amine and polyphosphoric acid are mixed
together and heated to about 90.degree.-100.degree. C. under
vacuum. The product thereof is thereafter cooled to 20.degree. to
90.degree. C., preferably to 30.degree. C., and thereto there is
added 50 to 100 mole %, preferably 90 to 100 mole %, of a
quaternizing agent, and the mixture is thereafter heated so as to
effect quaternization of the alkoxylated fatty acid amine. Any
unreacted quaternizing agent may be stripped away at elevated
temperature and under vacuum. The remaining product is thereafter
cooled and there is slowly added thereto the phosphating agent in
amounts of 10 to 200 mole %, preferably 90 to 110 mole %, at
temperatures of 20.degree. to 110.degree. C., preferably 40.degree.
to 50.degree. C. If phosphorus oxychloride acid is used as the
phosphating agent, the reaction mixture is bubbled with nitrogen at
such temperature until a desired degree of chloride ion is reached,
preferably 0.01 to 1.0%. The phosphorus oxychloride reaction
product is then drowned into water and base and there is thereafter
obtained the surfactant solution containing the instant
product.
The invention is further described with reference to the following
representative compositions and process for manufacture of the
same; the examples are not, however, intended to limit the
generally broad scope of the invention.
The nature of the invention may perhaps be best understood by the
detailed procedure set forth in the examples herebelow for
preparing a typical member of the phosphated quaternized
ethoxylated amphoterics; all parts, proportions and percentages in
these examples, as well as in the appended claims, are by weight
unless indicated otherwise. Ethylene oxide throughout these
examples is referred to as "EO".
EXAMPLE I
Charge into a 1-liter flask equipped with an agitator, thermometer
and gas inlet, 320 parts (0.5 mole) of cocoamine + 10EO and 2 parts
of 50% hypophosphorous acid. Dry the mixture under vacuum (10-15
mm.) at 80.degree.-100.degree. C. Cool under dry nitrogen to
40.degree.-50.degree. C. and add 80 parts (0.52 mole) of diethyl
sulfate at 40.degree.-50.degree. C. over two hours.
Strip any unreacted diethyl sulfate at 90.degree.-100.degree. C.
under good vacuum. Cool to 30.degree.-40.degree. C., and, under a
nitrogen blanket, add 35.5 parts of phosphorus pentoxide and stir
at 100.degree. C. for 5 hours. Cool to 80.degree.-85.degree. C.,
add 5 parts water, and stir for 2 hours. There is obtained 433
parts of active surfactant. This represents a 99% yield.
EXAMPLE II
Operating as in Example I, 460 parts (0.4 mole) of tallowamine
(Armeen-TD- a distilled tallow amine made by and available from
Armak) + 20EO and 2 parts of 50% hypophosphorous acid are charged
to a 1-liter flask. The mixture is dried at 90.degree.-100.degree.
C. under a good vacuum, cooled to 30.degree.-40.degree. C., and 60
parts of diethyl sulfate are added over 2 hours. The mixture of
quaternized amine ethoxylate is phosphated in the following manner.
Hypophosphorous acid (50%) 1 part, is added at 40-50.degree. C.
followed by 29 parts of phosphorus pentoxide at 50-60.degree. C.
The mixture is heated to 100.degree. C. for 5 hours under a
nitrogen blanket, cooled to 80.degree.-85.degree. C., and 5 parts
water are added. The system is stirred for 2 hours at
80.degree.-85.degree. C. There is obtained 553 parts of 100 %
active surfactant.
EXAMPLE III
According to Example I, 460 parts of tallowamine + 20EO, 2 parts of
50% hypophosphorous acid and 60 parts of diethyl sulfate are
reacted to form 520 parts of quaternized tallowamine + 20EO. To
this mixture, 1 part 50% hypophosphorous acid is added at
40.degree.-60.degree. C., followed by 170 parts of 115%
polyphosphoric acid at 40.degree.-60.degree. C. under a nitrogen
blanket. The phosphating mixture is heated at 100.degree. C. for 5
hours, then cooled to 80.degree.-85.degree. C., and 5 parts of
water are added. After two hours at 80.degree.-85.degree. C., 1
part of 35% hydrogen peroxide is added to yield 697 parts of 100%
active surfactant.
EXAMPLE IV
As in Example I, 586 parts of oleylamine + 7EO and 2 parts of 50%
hypophosphorous acid are dried and reacted with 286 parts of oleyl
chloride at 60.degree.-70.degree. C. for 10 hours. The quaternized
amine ethoxylate mixture is mixed with 1 part 50% hypophosphorous
acid and 28 parts water. Phosphorus pentoxide, 142 parts, is added
slowly under a nitrogen blanket at 40.degree.-50.degree. C. over 2
hours. The reaction mixture is heated for 3 hours at 90.degree. C.,
and then 5 parts of water are added. The resulting surfactant is
heated an additional 2 hours at 80.degree.-90.degree. C., cooled to
60.degree. C., and then 1 part 35% hydrogen peroxide is added.
There is obtained 1,042 parts of surfactant.
EXAMPLE V
As in Example I, 708 parts of stearyl amine + 10EO, 2 parts of 50%
hypophosphorous acid and 126 parts of benzyl chloride are reacted
at 70.degree.-80.degree. C. to form the quaternized amine
ethoxylate. This material is then reacted with 75 parts of
phosphorus oxychloride at 40.degree.-50.degree. C. over 4 hours.
The hydrogen chloride is removed by nitrogen bubbling to a constant
chloride ion content. The phosphated acid mixture was drowned into
120 parts of 50% caustic soda, to obtain 980 parts of surfactant
solution.
EXAMPLE VI
The following surfactant compositions can be employed for different
end uses, specified below, in accordance with the following table,
Table 1, wherein all parts mentioned are defined in terms of weight
%.
TABLE 1 ______________________________________ Liquid Hard Drain
Steam Surface Cleaner Degreaser Cleaner
______________________________________ Phosphate ester amphoteric
1.0 1.0 1.0 of Example I NaOH 9.0 17.0 2.0 TKPP -- -- 10.0 Water
90.0 82.0 87.0 Totals 100.0 100.0 100.0
______________________________________
EXAMPLES VII-XII
The present compounds are also applicable as alkaline hard surface
cleaners, exhibiting excellent caustic stability depending upon the
degree of ethoxylation, anionic functionality, and hydrophobe.
Alkali solubility is shown in Table 2.
TABLE 2 ______________________________________ Caustic Solubility -
1% Surfactant Soluble From 0 to 100.degree. C In (x) % NaOH Example
% No. COMPOUND NaOH ______________________________________ 7 Sodium
Phosphate of Cocoamine + 5EO diethyl sulfate 9.4 8 Sodium Phosphate
of Cocoamine + 10EO diethyl sulfate 6.6 9 Sodium Phosphate of
Cocoamine + 15EO diethyl sulfate 4.9 10 Sodium Phosphate of
Cocoamine + 20EO diethyl sulfate 4.25 11 Sodium Phosphate of
Cocoamine + 30EO diethyl sulfate 3.2 12 Sodium Phosphate of
Cocoamine + 50EO diethyl sulfate 2.4
______________________________________
EXAMPLE XIII
Fabric softeners and detergent/softeners and sanitizers can be
prepared for use on textiles, and Table 3 below sets forth typical
formulations (wherein all ingredients are in parts by weight %) for
such purposes:
TABLE 3 ______________________________________ 1 2 3
______________________________________ Present amphoteric
surfactant 3-7 10-30 10-30 Distearyl dimethyl -- 3-7 3-7 ammonium
halide (n-alkyl dimethyl benzyl -- -- 5-10 ammonium halide Sodium
acetate 1-2 -- -- Water to 100% to 100% to 100%
______________________________________
EXAMPLE XIV
This example is intended to show that the present surfactants can
be effectively employed in textile softening compositions. In this
example, 5 parts by weight of the present amphoteric surfactant in
95 parts by weight of water are neutralized with sodium hydroxide
to a pH of 5.5. This solution, as noted, is a very efficient
softener/antistatic agent for textiles.
In a typical application, the solution is diluted 1:10 with
distilled water.
Conventional textile fabric substrates are then treated with the
dilute surfactant solution during conventional padding of such
substrates. The fabrics thus softened show excellent softness,
i.e., pliable to feel, and complete elimination of static
electricity upon drying.
The advantage of this softener over conventional cationic softeners
is that it can be washed out during subsequent laundering, whereas
the cationic softeners tend to build up over repeated
applications.
EXAMPLE XV
In this example there were prepared, according to the procedure of
Example I (except for the identity and amount of amine reactant
used), (a) the sodium phosphate of tallowamine + 5EO diethyl
sulfate and (b) the sodium phosphate of oleylamine + 5EO diethyl
sulfate. With respect to (a) 240 parts by weight (0.5 mole) of
tallowamine + 5EO (Ethomeen T/15 of Armak) was used (instead of the
0.5 mole of cocoamine + 10EO of Example I), and, with respect to
(b), 250 parts (0.5 mole) of oleylamine + 5EO (Ethomeen 0/15 of
Armak) was used (instead of the 0.5 mole of cocoamine + 10EO of
Example I).
Then, 0.4% aqueous solutions of (a) and (b) were prepared, their pH
values were adjusted to pH 8.5 with triethanolamine, and the
pH-adjusted solutions evaluated for use as water-based lubricants.
The Falex Load Test was used to determine the lubricating
properties of the respective solutions, and the following results,
set forth below in Table 4, were obtained.
TABLE 4 ______________________________________ Sample Load at
Failure ______________________________________ (1) 0.4% aq. sodium
phosphate of tallowamine + 5EO diethyl sulfate 4,000 lbs. (2) 0.4%
aq. sodium phosphate of oleylamine + 5EO diethyl sulfate 4,250 lbs.
(3) Water (control) 550 lbs.
______________________________________
These results indicate excellent lubricant properties.
The products of the instant invention may also be further
compounded with other ingredients to provide for the following
uses:
Liquid steam cleaning compounds, floor maintenance products, wax
removers, automobile care products, waterless hand cleaners, oil
tank degreaser, aluminum cleaner, hand washing compound, sanitizing
hand dishwashing or light duty cleaning compound, pet shampoos, rug
and upholstery shampoos, mothproofing, and the like.
It is obvious that numerous changes and modifications can be made
in the invention without departing from the spirit and scope
thereof, and all such obvious modifications are considered to be
within the scope of the invention.
For example, in a preferred embodiment of this invention, it has
been previously stated that the desired end products comprise
mainly a monoester product and a diester product. As would be
apparent to those skilled in the art, in view of the foregoing
description of this invention, the monoester product would be
obtained predominately when about 2.0 moles of phosphating agent
were used per mole of quaternary alkoxylated monoalkyl amine.
Alternatively, the diester product would tend to be the major
product when about 1.0 moles of phosphating agent were used per
mole of quaternary alkoxylated monoalkyl amine. And likewise, the
triester product would tend to be the major product when about 0.5
mole of phosphating agent was used per mole of quaternary
alkoxylated monoalkyl amine. As one used an increasing excess of
phosphating agent beyond about 2.0 moles of phosphating agent, it
would be apparent to those skilled in the art that correspondingly
increased polymerization product would result. Thus, it can be seen
that obtainment of the numerous, varied types of phosphated
amphoteric product mixtures that are possible with the practice of
this invention can vary considerably within the scope of this
invention, as, e.g., with the amounts of phosphating and
oxyalkylating agents used, but all this would represent mere
routine experimentation by and to those skilled in the art.
* * * * *